Cheap Flights from Milan to Chicago, IL from $399
Return flight: Chicago – Milan
On Cheapflightsplus.com you will find 2 direct and 152 connecting flights from Milan to Chicago. You can compare airfare deals from 28 airlines and multiple travel sites from $399, book and save on cheap plane tickets and last minute offers. Also check out MIL-CHI flight schedule to find best flight time, convenient departure and arrival airports.
Find One-Way and Round-Trip Milan to Chicago Flight Deals
To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights».
To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight.
Cheapest flights in November: $399 (one-way), $684 (round-trip).
Direct flights
Check prices for return flight
Best Flights from Milan to Chicago Today
Take a look at the list of non stop flights and flights with layovers from Milan to Chicago with the lowest price of $399. The fastest direct flight takes 9h 50m and the fastest connecting – 12h 15m.
| Price | Departure | Arrival | Flight Duration | Airline | Flight |
|---|---|---|---|---|---|
| from $1481 | 15:20 Milan Malpensa | 18:10 Chicago O'Hare International | 9h 50m | Lufthansa | LH7812 |
| from $1550 | 15:20 Milan Malpensa | 18:10 Chicago O'Hare International | 9h 50m | United Airlines | UA415 |
| from $434 | 20:20 Milan Linate | 14:15+1 день Chicago O'Hare International | 24h 55m layover 12h 55m - Madrid | Iberia | IB666 AY5659 |
| from $448 | 11:20 Milan Linate | 19:00 Chicago O'Hare International | 14h 40m layover 3h 40m - Dublin | Aer Lingus | EI433 EI125 |
| from $469 | 14:55 Milan Malpensa | 14:15+1 день Chicago O'Hare International | 30h 20m layover 18h 15m - Madrid | Iberia | IB674 IB341 |
| from $517 | 19:05 Milan Malpensa | 14:15+1 день Chicago O'Hare International | 26h 10m layover 14h 5m - Madrid | Iberia | IB676 IB341 |
| from $540 | 06:50 Milan Malpensa | 17:55 Chicago O'Hare International | 18h 5m layover 3h 35m - Istanbul | Turkish Airlines | TK1878 TK5 |
| from $540 | 10:45 Milan Malpensa | 22:00 Chicago O'Hare International | 18h 15m layover 4h 0m - Istanbul | Turkish Airlines | TK1874 TK155 |
| from $540 | 20:10 Milan Malpensa | 09:40+1 день Chicago O'Hare International | 20h 30m layover 6h 20m - Istanbul | Turkish Airlines | TK1876 TK185 |
| from $540 | 06:50 Milan Malpensa | 22:00 Chicago O'Hare International | 22h 10m layover 7h 55m - Istanbul | Turkish Airlines | TK1878 TK155 |
| from $541 | 15:10 Milan Malpensa | 09:40+1 день Chicago O'Hare International | 25h 30m layover 11h 20m - Istanbul | Turkish Airlines | TK1896 TK185 |
| from $541 | 20:10 Milan Malpensa | 17:55+1 день Chicago O'Hare International | 28h 45m layover 14h 15m - Istanbul | Turkish Airlines | TK1876 TK5 |
| from $541 | 10:45 Milan Malpensa | 09:40+1 день Chicago O'Hare International | 29h 55m layover 15h 45m - Istanbul | Turkish Airlines | TK1874 TK185 |
| from $541 | 15:10 Milan Malpensa | 17:55+1 день Chicago O'Hare International | 33h 45m layover 19h 15m - Istanbul | Turkish Airlines | TK1896 TK5 |
| from $399 | 09:00 Milan Milan Bergamo (Orio al Serio) | 17:50 Chicago O'Hare International | 15h 50m layover 2h 0m - Warsaw 0h 45m - Helsinki | Wizz Air | W61432 AY1144 AY9 |
| from $403 | 08:30 Milan Malpensa | 17:25 Chicago O'Hare International | 15h 55m layover 1h 50m - Dusseldorf 0h 40m - Helsinki | EasyJet | U23025 AY1392 AY9 |
Show all tickets
*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on August 31, 2025
Flight Schedule Milan to Chicago (Illinois)
Full flight schedule will help you in detecting at what time planes fly from Milan to Chicago. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.
| Departure | Arrival | Flight Details | Flight Duration | Price |
|---|---|---|---|---|
|
15:20 — 18:10
|
15:20 — 18:10
LH7812
Lufthansa
Milan — Chicago
|
9h 50m |
Find flight
from$1481 |
|
|
15:20 — 18:10
|
15:20 — 18:10
UA415
United Airlines
Milan — Chicago
|
9h 50m |
Find flight
from$1550 |
|
|
06:50 — 17:55
|
07:00 — 12:00
TK1878
Turkish Airlines
Milan — Istanbul
3h 35m stop
15:30 — 18:25
TK5
Turkish Airlines
Istanbul — Chicago
|
18h 5m including layover |
Find flight
from$540 |
|
|
06:50 — 22:00
|
06:50 — 10:50
TK1878
Turkish Airlines
Milan — Istanbul
7h 55m stop
18:45 — 22:00
TK155
Turkish Airlines
Istanbul — Chicago
|
22h 10m including layover |
Find flight
from$540 |
|
|
07:25 — 13:50
|
07:25 — 08:30
BA561
British Airways
Milan — London
2h 35m stop
11:05 — 13:50
BA295
British Airways
London — Chicago
|
13h 25m including layover |
Find flight
from$560 |
|
|
07:50 — 14:15
|
07:50 — 10:10
IB668
Iberia
Milan — Madrid
1h 25m stop
11:35 — 14:15
AY5659
Finnair
Madrid — Chicago
|
13h 25m including layover |
Find flight
from$544 |
|
|
08:30 — 18:15
|
07:15 — 10:50
U23969
EasyJet
Milan — Reykjavik
5h 30m stop
16:45 — 17:20
FI853
Icelandair
Reykjavik — Chicago
|
16h 45m including layover |
Find flight
from$710 |
|
|
10:45 — 22:00
|
10:45 — 14:45
TK1874
Turkish Airlines
Milan — Istanbul
4h stop
18:45 — 22:00
TK155
Turkish Airlines
Istanbul — Chicago
|
18h 15m including layover |
Find flight
from$540 |
|
|
10:45 — 09:40
+1 day
|
11:10 — 16:10
TK1874
Turkish Airlines
Milan — Istanbul
15h 45m stop
07:35 — 10:10
TK185
Turkish Airlines
Istanbul — Chicago
|
29h 55m including layover |
Find flight
from$541 |
|
|
11:20 — 19:00
|
11:20 — 12:55
EI433
Aer Lingus
Milan — Dublin
3h 40m stop
16:40 — 19:00
EI125
Aer Lingus
Dublin — Chicago
|
14h 40m including layover |
Find flight
from$448 |
|
|
13:05 — 13:10
+1 day
|
13:00 — 14:10
AZ2133
Alitalia
Milan — Rome
19h 10m stop
09:25 — 13:10
AZ628
Alitalia
Rome — Chicago
|
31h 5m including layover |
Find flight
from$653 |
|
|
13:20 — 20:13
|
13:20 — 16:20
BA1623
British Airways
Milan — Philadelphia
2h 17m stop
18:45 — 20:22
BA5702
British Airways
Philadelphia — Chicago
|
13h 53m including layover |
Find flight
from$640 |
|
|
14:00 — 13:10
+1 day
|
14:00 — 15:10
AZ2049
Alitalia
Milan — Rome
18h 15m stop
09:25 — 13:10
AZ628
Alitalia
Rome — Chicago
|
30h 10m including layover |
Find flight
from$653 |
|
|
14:55 — 14:15
+1 day
|
14:25 — 16:50
IB674
Iberia
Milan — Madrid
18h 15m stop
11:35 — 14:15
IB341
Iberia
Madrid — Chicago
|
30h 20m including layover |
Find flight
from$469 |
|
|
15:10 — 09:40
+1 day
|
14:40 — 19:35
TK1896
Turkish Airlines
Milan — Istanbul
11h 20m stop
07:35 — 10:10
TK185
Turkish Airlines
Istanbul — Chicago
|
25h 30m including layover |
Find flight
from$541 |
|
|
15:10 — 17:55
+1 day
|
14:40 — 19:35
TK1896
Turkish Airlines
Milan — Istanbul
19h 15m stop
15:30 — 18:25
TK5
Turkish Airlines
Istanbul — Chicago
|
33h 45m including layover |
Find flight
from$541 |
|
|
17:00 — 13:10
+1 day
|
17:00 — 18:10
AZ2061
Alitalia
Milan — Rome
15h 15m stop
09:25 — 13:10
AZ628
Alitalia
Rome — Chicago
|
27h 10m including layover |
Find flight
from$653 |
|
|
19:00 — 13:10
+1 day
|
19:00 — 20:10
AZ2109
Alitalia
Milan — Rome
13h 15m stop
09:25 — 13:10
AZ628
Alitalia
Rome — Chicago
|
25h 10m including layover |
Find flight
from$653 |
|
|
19:05 — 14:15
+1 day
|
19:05 — 21:30
IB676
Iberia
Milan — Madrid
14h 5m stop
11:35 — 14:15
IB341
Iberia
Madrid — Chicago
|
26h 10m including layover |
Find flight
from$517 |
|
|
20:20 — 14:15
+1 day
|
20:25 — 22:50
IB666
Iberia
Milan — Madrid
12h 55m stop
11:35 — 14:30
AY5659
Finnair
Madrid — Chicago
|
24h 55m including layover |
Find flight
from$434 |
|
|
20:20 — 14:15
+1 day
|
20:20 — 22:40
IB666
Iberia
Milan — Madrid
12h 55m stop
11:35 — 14:15
IB341
Iberia
Madrid — Chicago
|
24h 55m including layover |
Find flight
from$523 |
|
|
08:30 — 17:25
|
07:00 — 08:35
U23025
EasyJet
Milan — Dusseldorf
1h 50m stop
11:55 — 15:20
AY1392
Finnair
Dusseldorf — Helsinki
40m stop
16:25 — 17:50
AY9
Finnair
Helsinki — Chicago
|
15h 55m including layover |
Find flight
from$403 |
|
|
09:00 — 17:50
|
09:00 — 11:00
W61432
Wizz Air
Milan — Warsaw
2h stop
13:00 — 15:40
AY1144
Finnair
Warsaw — Helsinki
45m stop
16:25 — 17:50
AY9
Finnair
Helsinki — Chicago
|
15h 50m including layover |
Find flight
from$399 |
|
|
09:15 — 19:40
|
08:55 — 10:40
W45018
Aero Services Executive
Milan — Tirana
2h 30m stop
13:30 — 15:35
LO598
LOT
Tirana — Warsaw
1h stop
16:40 — 20:00
LO3
LOT
Warsaw — Chicago
|
17h 25m including layover |
Find flight
from$571 |
|
|
11:55 — 21:00
|
11:55 — 13:50
W45024
Aero Services Executive
Milan — Tirana
1h 15m stop
15:05 — 16:05
JU163
Air Serbia
Tirana — Belgrade
1h 15m stop
17:20 — 21:00
JU506
Air Serbia
Belgrade — Chicago
|
16h 5m including layover |
Find flight
from$560 |
|
|
12:15 — 09:40
+1 day
|
12:15 — 13:40
FR2285
Ryanair
Milan — Naples
2h 20m stop
16:00 — 19:25
TK1464
Turkish Airlines
Naples — Istanbul
11h 5m stop
06:30 — 09:40
TK185
Turkish Airlines
Istanbul — Chicago
|
28h 25m including layover |
Find flight
from$722 |
|
|
12:15 — 09:40
+1 day
|
12:15 — 13:40
FR2285
Ryanair
Milan — Naples
7h stop
20:40 — 00:05
TK1880
Turkish Airlines
Naples — Istanbul
6h 25m stop
06:30 — 09:40
TK185
Turkish Airlines
Istanbul — Chicago
|
28h 25m including layover |
Find flight
from$722 |
|
|
18:30 — 19:40
+1 day
|
18:30 — 19:55
FR1533
Ryanair
Milan — Vienna
13h 20m stop
09:15 — 10:30
LO224
LOT
Vienna — Warsaw
6h 10m stop
16:40 — 19:40
LO3
LOT
Warsaw — Chicago
|
32h 10m including layover |
Find flight
from$724 |
|
|
22:15 — 18:15
+1 day
|
22:15 — 23:45
EI437
Aer Lingus
Milan — Dublin
9h 5m stop
08:50 — 10:20
EI156
Aer Lingus
Dublin — London
5h 10m stop
15:30 — 18:15
EI8997
Aer Lingus
London — Chicago
|
27h including layover |
Find flight
from$695 |
|
|
22:15 — 18:15
+1 day
|
22:15 — 23:45
EI437
Aer Lingus
Milan — Dublin
6h 45m stop
06:30 — 08:00
EI152
Aer Lingus
Dublin — London
7h 30m stop
15:30 — 18:15
EI8997
Aer Lingus
London — Chicago
|
27h including layover |
Find flight
from$695 |
|
|
23:50 — 15:55
+1 day
|
23:10 — 00:45
W64124
Wizz Air
Milan — Belgrade
8h stop
09:25 — 11:20
LX1413
SWISS International Air Lines
Belgrade — Zurich
1h 45m stop
13:05 — 15:55
LX8
SWISS International Air Lines
Zurich — Chicago
|
23h 5m including layover |
Find flight
from$753 |
|
*Departure and arrival times - local. Updated on August 31, 2025
Flight Information
Below we will explain in detail what the flights cost on the destination from Milan to Chicago depends on and how to choose the most interesting flight option for you.
Distance between Milan and Chicago is 7289 miles. Time difference between the cities is 7h. Airplanes depart 05:25 to 23:59 from 4 Milan airports and arrive 05:25 to 23:59 to 7 Chicago airports. Average flight time is 9h 50m.
- The fastest flight 9h 50m
- Average flight time 9h 50m
- The earliest flight 05:25
- The latest flight 23:59
- Distance 4530 ml
The cheapest months to travel to Chicago are august (from 399 $), september (from 434 $), october (from 448 $).
The most expensive months are december (from 644 $), january (from 643 $), november (from 642 $).
What is the lowest airfare Milan to Chicago?
The cheapest plane ticket found by our users is $399. This airfare is for economy class on one-way W61432 flight by Wizz Air for July 13, 2025 which leaves Milan Bergamo (Orio al Serio) in Milan at 09:00 am and arrives at Chicago O'Hare International at 17:50.
Economy class
$399
Business class
?
First class
?
Popular Airlines on the Route
The flight Milan — Chicago is served by 28 regular airlines and 5 low-cost airlines. Most of the flights on this route are operated by Neos - 4 departures per week at the price of from $ 818 . And the most expensive tickets are offered by British Airways airline - from $ 1874.
Direct flights
There are 2 nonstop flights on the route. The fastest direct flight is LH7812 by Lufthansa takes 9h 50m and the cheapest is W61432 by Wizz Air for $1481.
- LH - Lufthansafrom $1481Find
- UA - United Airlinesfrom $1550Find
See more direct flights
Connecting Flights
There are 152 flights with layovers on the route. The fastest connecting flight is AF1213 by Air France takes 12h 15m and the cheapest is W61432 by Wizz Air for $399.
- NO - Neosfrom $818Find
- LO - LOTfrom $880Find
- VY - Vuelingfrom $935Find
- FI - Icelandairfrom $1030Find
- JU - Air Serbiafrom $829Find
- FR - Ryanairfrom $701Find
- LX - SWISS International Air Linesfrom $727Find
- A3 - Aegean Airlinesfrom $800Find
- DY - Norwegianfrom $696Find
- SK - SASfrom $752Find
- IB - Iberiafrom $434Find
- KL - KLMfrom $754Find
See more connecting flights
Airports
You can fly from Milan to Chicago from 4 airports (Linate, Malpensa, Milan Bergamo (Orio al Serio), Segrate).
Milan airports
- Linate-LINfrom $434Find
- Malpensa-MXPfrom $403Find
- Milan Bergamo (Orio al Serio)-BGYfrom $399Find
- Segrate-SWKFind
Chicago airports
- O'Hare International-ORDFind
- Midway-MDWFind
- Dupage County-DPAFind
- Chicago FSS-CHIFind
- Merrill C Meigs (closed)-CGXFind
- Pal-Waukee-PWKFind
- Chicago NAS-NOHFind
Airplanes
There are flights to Chicago from Milan by 28 airlines that use 0 aircraft brands. They range from huge modern airplanes to small-sized.
Top International Destinations from Milan
Our state-of-the art metasearch will definitely provide you with the best airfare on international flights. We’re proud to partner with many reliable travel suppliers located outside the US what gives us an opportunity to offer the most competitive prices on far destinations.
- from $59Find
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- from $56Find
How to book a plane ticket yourself?
- Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
- Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
- Click «Buy» when you are ready — our system will redirect you to the site that sells the selected flight ticket.
- Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
- That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.
To find a plane ticket, please select dates.